From Mystic River to One Battle After Another: Sean Penn’s Extraordinary Oscar Arc

Few actors have traveled as far within the Academy Awards as Sean Penn. His first win — for Mystic River in 2004 — established him as the defining screen actor of his era. His second — for Milk in 2009 — confirmed it. And his third — for One Battle After Another at the 2026 ceremony — completed one of the most remarkable Oscar arcs in film history, placing him alongside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis as the most decorated male acting performers the Academy has ever recognized.
The 98th Oscars ceremony, held at the Dolby Theatre, was notable not only for the win but for the winner’s absence. Penn was not at the ceremony when his name was announced as Best Supporting Actor, leaving presenter Kieran Culkin to collect the award and offer a dry, well-received explanation. The crowd responded with both laughter and heartfelt applause for an achievement that, absent or not, demanded recognition.
In One Battle After Another, Penn portrays a military officer whose dogma becomes his defining and most destructive characteristic. The performance has been widely praised as one of the finest of the year and a career highlight for an actor already rich in those. Director Paul Thomas Anderson had his own career-defining night, winning both Best Adapted Screenplay and Best Director — his first Oscars — completing a triumphant chapter in a career long celebrated by critics but previously ignored by the Academy.
Conan O’Brien presided over the evening with a deft hand, blending sharp humor with genuine feeling. His opening monologue touched on artificial intelligence, the future of entertainment, and the global power of cinema. With nominees representing 31 countries and six continents, the ceremony reflected a world in which film truly has no borders.
Michael B. Jordan rounded out the night with a Best Actor win for Sinners, defeating Leonardo DiCaprio in one of the evening’s closest races. From start to finish, the 2026 Academy Awards delivered on every level — except for the small matter of Sean Penn’s empty seat.